Middlebury vacation rentals

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Best Middlebury vacation rentals

Most recommended vacation rentals in Middlebury

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The Wellington Lake Cottage - Middlebury - Balcony
The Wellington Lake Cottage
Middlebury, IN
9.0Wonderful(13)
Parking
Free Wi-Fi
$123+
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Hot Tub|beauitiful Backyard Oasis|newly Renovated - Middlebury - Living room
Hot Tub|beauitiful Backyard Oasis|newly Renovated
Middlebury, IN
$536+
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Lakin' It Easy - Middlebury - Balcony
Lakin' It Easy
Middlebury, IN
9.3Wonderful(13)
$222+
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Charming Middlebury Retreat with Patio and Fire Pit - Middlebury - Living room
Charming Middlebury Retreat with Patio and Fire Pit
Middlebury, IN
Free Wi-Fi
$346+
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Stone Lake Vacation Cottage Middlebury, IN Boat Kayak Fishing Swimming getaway - Middlebury - Balcony
Stone Lake Vacation Cottage Middlebury, IN Boat Kayak Fishing Swimming getaway
Middlebury, IN
Free Wi-Fi
$239+
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| Hot Tub | Amish Farm Country | Pergola | Deck | - Middlebury - Living room
| Hot Tub | Amish Farm Country | Pergola | Deck |
Middlebury, IN
Free Wi-Fi
$243+
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Charming, spacious home near towncenter amenities, resturants, trails and parks. - Middlebury - Dining room
Charming, spacious home near towncenter amenities, resturants, trails and parks.
Middlebury, IN
Free Wi-Fi
$194+
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Game Room | Pool Table | Foosball|Family Focused| - Middlebury - Living room
Game Room | Pool Table | Foosball|Family Focused|
Middlebury, IN
$264+
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`Burning Pine Inn' Farm House in Amish country. - Middlebury - Living room
`Burning Pine Inn' Farm House in Amish country.
Middlebury, IN
$450+
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Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury - Middlebury - Kitchen
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury, IN
Free Wi-Fi
$165+
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Cozy, peaceful 2nd level apt-close to Toll Rd - Middlebury
Cozy, peaceful 2nd level apt-close to Toll Rd
Middlebury, IN
$177+
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Adjoining apts - main & 2nd level - Middlebury
Adjoining apts - main & 2nd level
Middlebury, IN
$285+
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Peaceful apt in the country-close to Shipshewana - Middlebury
Peaceful apt in the country-close to Shipshewana
Middlebury, IN
Free Wi-Fi
$178+
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Escape To Amish Country For Some R&rx - Middlebury
Escape To Amish Country For Some R&rx
Middlebury, IN
$209+
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That Pretty Place Bed & Breakfast - Middlebury
That Pretty Place Bed & Breakfast
Middlebury, IN
9.6Wonderful(42)
Free Wi-Fi
$81+
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Waterfront Retreat, 10 Mi to Dtwn Shipshewana - Middlebury
Waterfront Retreat, 10 Mi to Dtwn Shipshewana
Middlebury, IN
9.7Wonderful(15)
$375+
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$81 - $195$195 - $309$309 - $423$423 - $536$536+ per night

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Free cancellationFree breakfastFree parkingFree internet
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Good to know

Low season

December

High season

November

Average price (weeknight)

$117

Average price (weekend night)

$278
Cheapest month to stay with an average 52% drop in price.
Most expensive month to stay with an average 158% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Middlebury vacation rental deals

  • Vacation rentals in Middlebury are around 54% more expensive than hotels on average. Search here to compare prices for all accommodation types in Middlebury.
  • The best vacation rental properties in Middlebury are Charming 1912 Bungalow in Middlebury Indiana (10.0, 26 reviews), | Hot Tub | Amish Farm Country | Pergola | Deck | (9.9, 41), and Charming, spacious home near towncenter amenities, resturants, trails and parks. (9.9, 50), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Middlebury, you should consider visiting during the low season. The cheapest vacation homes in Middlebury can be found in December and August.
  • The cheapest night for renting a vacation home in Middlebury is Tuesday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Middlebury for 3 days.

FAQs when booking a vacation home in Middlebury

  • What types of vacation rentals are available in Middlebury?

    There are loads of different property types that you can make your vacation home in Middlebury. You’ll find apartments and houses.

  • Are there any pet-friendly vacation rentals in Middlebury?

    There are a number of dog and pet-friendly Middlebury vacation rentals, with around 4% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Middlebury?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Middlebury?

Our map will help you find the perfect place to stay in Middlebury by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Middlebury

Middlebury vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Middlebury. Find cheap vacation homes to rent in Middlebury. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Middlebury that suits you best.

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